


Dressup

by DangerRollins



Category: The Walking Dead (TV)
Genre: (mentioned) - Freeform, Blow Jobs, Crossdressing, Daddy Kink, M/M, Makeup, Motorcycle Sex, Sex Toys
Language: English
Status: Completed
Published: 2018-06-26
Updated: 2018-06-26
Packaged: 2019-05-29 02:51:42
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,132
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15063404
Author URL: https://archiveofourown.org/users/DangerRollins/pseuds/DangerRollins
Summary: Carl decides to dress up for Negan, and damn if he isn't glad that he did.





	Dressup

**Author's Note:**

> Damn, don't I feel fuckin' scandalous for writing this shit. I think it's good! I'm proud! Just a fair warning, the daddy kink is strong in this one, Carl will be wearing female clothing, and there are some sex toys in the mix! If you're not into some of that, you're gonna wanna skip this one.

Carl readjusted his position on the large bed for the thousandth time in the last ten minutes. He sat on his knees, making sure that his posture was straight and his head was held high. He glanced down and picked at a piece of lint that had landed on the fabric of his skirt before clearing his throat and looking back up again, staring at the door with determination in his eyes, willing it to just open up already and willing it to stay closed forever at the same time.

He let out a deep breath before glancing toward the large mirror that took up the entirety of the wall on the left side of Negan's room. He eyed himself, tilting his head a little as he wondered if he was about to make a humongous fool out of himself or if he was about to make Negan cum in his pants within the five seconds it'd take him to look him over.

Negan had always said he'd love to see Carl in women's clothing. He always told Carl that he'd love to see him in something sexy, like a short dress and some high heels or maybe a crop top and booty shorts. He'd been saying it for the longest, but Carl let it go in one ear and out the other.

Originally, he'd assumed Negan was joking. Negan always made crude comments, always jokingly emasculating him, and it never seemed to mean anything until suddenly it did. Suddenly the joking tone in his voice was gone as well as the amusement in his eyes as he said it. Negan was serious. This was what he actually, legitimately wanted.

Carl came to that realization at least three months ago. He didn't know what to say or what to do or how to react. He wasn't judging Negan, of course he wasn't. He couldn't. Carl himself had some pretty odd kinks, ones way weirder than this one—Not that it was really weird!— He just...He couldn't see himself dressed up in women's clothing and he didn't know what it'd mean.

'If Negan wants a woman, why isn't he with one? Why is he screwing around with me?' That was the first question that had run through Carl's mind as he thought more about the subject. 'Does he want me just to dress up like a lady or does he want me to act like one too?' That was the second.

It'd taken a long while for Carl to come to the conclusion that he was willing to try this out. He thought he might look damn stupid walking around dressed up like a girl, but if that's what Negan wanted then yeah, he'd try it. Negan had tried all sorts of shit for Carl, and he'd always ended up enjoying it, in the end, no matter how skeptical he'd been of it originally. Carl thought that maybe this would end the same.

So, here he was, on Negan's bed wearing nothing but long black socks, a black and blue plaid skirt, and a black bralette. He'd even made sure to brush his hair so that it was perfect and silky looking, and he'd also went out and bought some makeup. He stuck to the bare minimum, not able to do anything too drastic. Getting the eyeliner on had taken twenty minutes itself because he'd always been scared of things getting too close to his eyes and—And didn't parents and teachers and every other sane adult always used to tell him **not** to put sharp objects near his eyes? Especially not pencils!—But whatever, it's alright if it makes your eyes pop, he guessed.

He had to say, he did kind of enjoy the makeup. It was alright once you got used to it and it made him feel pretty. The red lipstick he'd applied made his lips appear even fuller, and the highlighter he'd made sure to add to his cheekbones made him feel like a diamond sticking out from beneath a bunch of old, dull rocks. He was dazzling and not to mention valuable. It was nice.

The clothes weren't so bad either, really. He felt sexy showing off his midriff and so much of his legs. The thin material of the skirt resting against his skin and caressing it ever so softly every time he moved reminded him of Negan's gentle touches. The skirt kept riding up, threatening to show off his otherwise uncovered cock, and that thought alone was enough to turn him on. He imagined going out in public wearing the skimpy piece of clothing. A small gust of wind would expose him, just like that.

He was kind of really starting to understand why Negan had wanted to see him like this so much.

Carl let out a soft gasp as he heard the sound of the front door opening. Within a matter of seconds, Negan would appear, and he'd see the way Carl was dressed, and he'd say something about the way that Carl was dressed, and Carl desperately hoped that whatever he said would be nice.

Negan was always giving him compliments, always making Carl feel confident--Maybe too confident at times--and Carl had no doubt that Negan would be considerate of his feelings, and whether he liked what he was wearing or not, he wouldn't be rude about it. Still, Negan could be pretty blunt at times too, and Carl really wanted him to like this. He'd dressed like this to please the other man. If Negan wasn't pleased with this then what was the point? Carl needed the man to like this, especially now that he'd realized how much he liked it himself.

Carl's breath caught in his throat as he watched the door handle slowly turn. Moments later, Negan was peeking inside, a large, wolfish grin on his face. He'd been out all day, running errands and attending to his bike shop, and he was happy to finally be home again.

Carl didn't move, blink, or breathe as Negan walked into the room, a shocked facial expression on his face. Negan was silent for a long while as he studied Carl. He took his time, allowing his eyes to take in every little detail of the ensemble Carl had put together. It took a good minute for him to say anything, and it felt like an hour to Carl.

"Hot damn! I am a lucky bastard, yes I motherfucking am!" Negan grinned largely as he continued to look at Carl, his eyes refusing to leave the boy's legs. "Don't you fucking look like a good little school girl or some type of god damn skater chick that's sucked a hundred dicks before and--"

"So, you like it?" Carl tried to make it come out like a sarcastic statement, but it sounded more like a pathetic question. He mentally cursed himself as he cleared his throat and looked down, pawing at some of his hair to get it out of his eyes. Negan's eyes softened as he stared at Carl for a few seconds before slowly walking toward the nervous boy. He reached a hand out to stroke the boy's jaw and then lifted his chin up, waiting for his large blue eyes to meet his own hardened hazel ones. "Were you sitting here all day, worried about what I'd think about this, kitten?"

Carl wanted to curse at him for calling him kitten as he usually would, but he only swallowed and searched Negan's eyes for comfort, which he found without a problem. He gave a small, shaky smile and shrugged his shoulders. "Not all day." He mumbled, his blush creeping down his neck.

"You know I think you're fucking adorable no matter what you wear, darling. You could wear a trash bag and my dick would still love your asshole just the fucking same."

"How romantic. Thanks, Negan." Carl rolled his eyes before straightening his posture, his tongue poking out between his lips as he furrowed his brows. "Well?"

"Well?" Negan raised his brows. Carl pouted.

"Well, I got all dressed up for you. Don't I get something in return? A reward?"

"You want me to wear a skirt?"

Carl scrunched up his face and shook his head quickly. Negan didn't have the calves for a skirt.

"I thought that maybe...Maybe you'd wanna...You know..." Carl looked down, his cheeks growing a deeper shade of red, and Negan quickly lifted his chin once again. "You know if you want something you've gotta ask for it." He told the pale boy sternly.

"I-I want you to fuck me." Carl squeaked. "Please?"

Negan leaned back and poked his tongue between his teeth as he stared at Carl. Fuck yes, he wanted to fuck the shit out of him. He looked god damn gorgeous, like some type of fucking angel sent straight from the devil down under, and Negan wanted to pound his little ass until he was begging for mercy and chanting the prayers his mama had probably taught him when he was younger, but Carl had asked for a reward, and yeah, he was gonna fucking get one.

There was nothing more rewarding than Negan's dick, he was sure of it, but this was a special occasion, so he'd save his cock for last and bring the toys out now.

Negan squatted down and rubbed Carl's cheek softly, smiling as the boy nuzzled his face into the palm of his hand, staring at him with curiosity dancing in his eyes. "Oh, fuck you I motherfucking will, Carl, but we'll get to that later. Right now, I want the focus to be all on you, so why don't we pick out a few toys for you to play with while daddy watches?"

Carl could complain about Negan referring to himself as daddy while they were in front of other people or casually lounging on the couch all he wanted to, but when they were in Negan's room, temperature rising as they stared at each other, excitement building in the pit of their stomachs because of what they knew was about to happen, the word only caused a surge of electricity to run through the veins in his cock.

He nodded slowly, eyes wide and lips parted, interest taking over him as he watched Negan make his way to his closet. A billion different thoughts ran through Carl's mind at once as he wondered what Negan had planned for him. Anything would do just fine, Carl wasn't picky with pleasure, and Negan always made sure to take care of him no matter what. Carl trusted Negan 100%; Whatever he decided on would be good.

After a few moments of digging around, Negan pulled out a large, black crate. Carl had seen it several times before, but the excitement threatening to bubble over in his stomach never went away no matter how many times he saw it. At first, he'd been skeptical of that crate, and he'd thought it was silly that Negan kept the crate--The same one that school teacher's had planted all over their rooms, filled to the brim with paperwork and crayons and glue and scissors and all sorts of other materials--full of sex toys, but eventually, it didn't matter to him. All that mattered was what was **inside** the damn thing.

Negan lifted it up effortlessly and brought it over to the bed, placing it right in front of Carl and sending him a bright smile as he did it. "Well, don't just stare at it," He chuckled after a moment, watching as Carl eyed it cautiously. "Pick three."

Carl's eyes widened as he snapped his eyes away from the large crate and towards Negan. Negan nodded at him and he slowly turned to peer inside of it. Usually, it was Negan who decided on what toys they'd use, and Carl had always loved everything he chose, but he also always wanted to pick out his own toys. Now that he was getting the chance to, he kind of wished Negan was the one making the big decision.

He hummed softly and tilted his head as he thought about what he wanted for a moment, and then he smirked as it came to him. He grabbed three things from the very top of the crate, just his blindfold--Customized with Negan's name on it--his favorite, furry, matching black handcuffs and the pastel pink vibrating cock ring that he'd taken an immediate liking to.

He held all the items out to Negan and smiled, blinking up at him innocently, though Negan saw right through him. The older man narrowed his eyes as he took the items into his hands. "Just these? No butt plug, no vibrator--Nothing?"

"I was thinking...Maybe you could let me...Let me use the hot seat?"

Carl fluttered his eyelashes and Negan chuckled as he realized what he wanted.

A couple months ago, Negan had been shopping online for some more toys, wanting to spice their sex lives up even further when he came across something called a deluxe hot seat. A vibrating cushion with a vibrator right in the middle for the young boy to ride, Carl had fallen in love with the toy the first time he'd used it. Negan had only allowed him to use it twice before, insisting on saving it for special occasions since he knew just how much Carl loved it.

Negan had deemed this a special occasion, so why the hell not?

He grinned and nodded at Carl before patting his head gently. "I'll go get it. As much as I hate to see that skirt go, it's kind of fucking got to. I'm gonna need you to take that off. Just that, nothing else."

Carl nodded obediently and watched as Negan left the room to go retrieve his favorite toy. He'd started storing it somewhere secret after he'd discovered Carl using it without his permission once. Carl could almost still feel the spanking he got for that.

Carl slowly shimmied his way out of the skirt, giggling as he thought about all the fun he was about to have.

Carl was sitting on the edge of the bed, grinding against it slowly as he bit the tips of his fingers in anticipation when Negan finally came back. He placed the toy down in the middle of the floor, right across from the bed, and got it set up and lubed up before finally finding his way back to Carl.

He hummed in approval before gently placing the blindfold over the boy's eyes, and then sliding the cock ring over his already dripping cock. He chuckled upon noticing how excited Carl was and gave the boy a gentle squeeze and stroke, causing him to suck in a sharp breath.

Negan grabbed Carl's hands and cuffed them together behind his back before helping the boy stand up and walk toward the hot seat. He positioned him over it and slowly lowered him down onto the toy. The loud whine Carl let out as he sunk down onto the large plastic cock made Negan's cock twitch with interest. Negan pressed the button on the boy's cock ring and watched as his hips jolted forward in response.

Negan stepped away and sat down on the edge of the bed, taking in the beautiful sight of Carl's body, back arched and stomach poking out as his lips formed a beautiful pout. He bit his lips as he palmed his own erection through his jeans, unzipping them to relieve just a little bit of the pressure he was feeling.

He grabbed the remote and turned the vibrator on to the lowest setting, smirking as Carl let out another long whine, almost a whimper.

"Do you want a higher setting, baby boy?" Negan questioned softly, eyes frantically moving from one spot of Carl's body to another until finally, they landed on his mouth, now wide open. Carl nodded quickly, licking his lip as he started to grind on the seat, pushing the vibrator deeper into himself as he did. "Yes, please."

"You're gonna have to earn it," Negan mumbled, thumb tapping on the side of the remote slowly. "Why don't you tell me how you finally decided on dressing up for me, hmm? You seemed pretty opposed to it a few weeks ago."

"I was curious about what it'd be like, what it'd feel like, and how I'd look," Carl nearly whispered. "You've tried a lot of stuff for me so I figured I should try this out for you, and I'm glad I did. I-I like it." If Carl's hands weren't behind his back he'd run his fingers along the thin material of his knee socks.

"Yeah?"

"Yeah. I like wearing these clothes. They make me feel confident. Sexy." Carl grinned as he furrowed his brow, the cock ring sending tingles all through his cock. "Do you like them, Negan? Really?"

"I do, honey," Negan smiled, eyes softening as he did. "You looked so amazing in that skirt I just wanted to rip it off of you!"

"Good," Carl breathed. "I wanted to make you happy, daddy."

Negan's breath caught in his throat as the word slipped so effortlessly off of Carl's tongue. They'd been together for a while now, and Carl had been calling him daddy for months now, but he never got used to the sweet sound of it.

"You made daddy very happy, sweetheart." And Negan made sure that Carl knew that by turning the intensity up just a little bit. Carl let out what Negan could only describe as a mewl and slowly began to lift himself up before sinking down onto the toy once again.

Negan watched silently as Carl rode his toy, skin flushing more than it had been already as he made a show of bouncing up and down on it quickly, grinding his body in a way that made Negan's cock feel like it was about to burst, and arching his back while throwing his head back to expose his neck, which was Negan's weakness, oddly enough. He was always touching Carl's neck or leaving slow, sweet kisses along it. He loved marking his boy by leaving small purple lovebites all along his thin neck, wordlessly telling the whole world that Carl belonged to him.

Negan removed his clothes and turned the toy up to its highest intensity, watching as the young boy writhed around and cried out his name over and over again as the toy continued to vibrate inside of him, clearly massaging his G-spot. Negan figured that if he didn't have his cock ring on, Carl would've come already. It wouldn't take him all that long as he'd obviously been excited all day, and the hot seat always got him off pretty quickly. Negan's eyes flickered down to Carl's cock, in all it's glistening pink glory. He looked as if he was about to burst, cock ring or not, and Negan licked his lips hungrily before slipping down to his knees and slowly crawling toward Carl.

Seconds later, Carl nearly screamed as he felt Negan's warm mouth wrapping around his throbbing cock. Negan wasn't big on giving blowjobs--not that Carl minded one bit as he made sure to make up for it in **other ways** \--but when he did--Shit. It was fucking god damn magical in Carl's humble ass opinion.

"F-Fuck, yes," Carl whimpered, tears welling up in his eyes as he tried to keep himself upright. His bouncing had come to an abrupt stop as soon as Negan had swallowed his cock. Now his energy was being spent on trying not to pass out as the pleasurable feeling of Negan's tongue swirling around the tip of his head took him over. "Daddy--So fucking good, so fucking--mgh!" Carl cursed himself for picking out handcuffs. If he hadn't, he would've been able to run his fingers through Negan's hair as he so often did to him.

Carl's stomach clenched and unclenched as he panted harshly, eyes rolling into the back of his skull as he focused on nothing but the feeling of Negan's tongue trailing the underside of his cock and the vibrator still pounding the shit out of his G-spot. He was thankful when he felt Negan's fingers fumbling with his cock ring, turning it off and then slipping it off just as easily as he'd put it on. He wasn't sure how much longer he could take not being able to cum, but now he didn't have to worry about it.

"C-Can I--"

Negan tapped Carl's thigh and nodded a little as he flattened his tongue and waited patiently for Carl to cum. He did in a matter of seconds, filling Negan's mouth up with his seed as he cried out the man's name along with a few incoherent curses. Negan hummed as he bobbed his head up and down Carl's length a few more times for good measure, slicking the boy's cock up with his own juices, and then pulled his mouth off with a pop.

Negan turned the vibrator down before turning it off, lifted the blindfold so that it was resting on Carl's head and then stroked Carl's thigh slowly and swallowed all of his delicious cum, watching closely as the boy's eyes drooped as they always did after he'd come especially hard. He grinned lazily at Negan, blinking tiredly at him, and then his eyes drifted down to focus on Negan's own erection.

"Do you want me to take care of that?" Carl asked, tilting his head slightly.

"Only if you want to, sweetheart."

"I do." Carl nodded, an adorable look of determination coming onto his face as he slowly stood up and stalked toward the bed. He ushered for Negan to come over and sit down, and the other man obliged without any complaint, taking his spot on the edge of the bed again. Carl sunk down to his knees in between Negan's legs and Negan pulled his blindfold down again, Carl smirking as he did.

Negan guided his cock into Carl's mouth, letting out a hiss as Carl immediately got to work, allowing his tongue to trace every single vein that he could find on Negan's cock before finally, he allowed his mouth to go slack. Negan took the hint and placed a firm hand on the back of Carl's head, guiding it forward so he could take more of him into his mouth.

Carl moaned as Negan's slow and patient pushing became needy and harsh. He'd always loved when Negan fucked his face, especially when he was blindfolded and restrained. It made him feel like a real slut; Some toy for Negan to play with until he was bored of it, and for some reason that made Carl's cock come to life once again.

Negan squeezed his eyes shut tightly, cursing insistently as the head of his cock repeatedly brushed up against the back of Carl's throat. Carl was moaning like a little slut once again and Negan sucked in a sharp breath as all his muscles tensed. He pushed Carl's face down until his nose was buried in his dark pubic hair and then came with a loud groan. Carl gagged only a few times, and Negan held him in place even while he did, knowing that he could take it.

When he was done coming, Negan slowly removed his hand from Carl's hair and watched as the boy removed his mouth from his cock, red lipstick smudged, saliva and cum dribbling down his chin as he swallowed what hadn't escaped his mouth and then grinned. "Good?" He questioned softly.

"Very good." Negan nearly cooed.

Negan removed Carl's blindfold before reaching around to uncuff him and then guided the boy onto the bed. They lied there side by side, silence taking over the room for a few moments before Negan decided to break it.

"Thank you," he muttered. "You looked gorgeous in those clothes, you know?"

"Thanks, daddy," Carl grinned. "I love you."

"I love you too, darling."

"...We're not done right?"

"What?"

"I still want you to fuck me." Carl blushed. Negan chuckled and shook his head at the boy. "Give me a few minutes, and then fuck you I most certainly motherfucking shall."

Carl grinned as he rested his chin on the palm of his hand, propping himself up as he stared at Negan. "You know what I think would be cool?" He questioned. Negan raised a brow as a small smirk made its way onto his face. Carl had mischief in his eyes and that always turned out to be a good thing for him. "What?" He asked.

"Maybe I could wear some lingerie for you. Maybe...Something with lace? Or silk? All black, obviously. Or maybe blue, cause it'd bring out my eyes...I wanna wear it under some really sexy clothes like maybe a mini skirt or something? A leather mini skirt. And your leather jacket." Carl giggled as Negan stared at him, pupils dilating seemingly with every word. "Ooh, what if I come to your shop wearing that? I bet it'd be really cool to be there with you all day, teasing the hell out of you. I'd be good, obviously. I'd just sit in a corner and do some paperwork or something, but I bet you'd spend the whole day staring at me. And you know I can never sit with my legs closed for too long, so I'm sure I'd end up flashing you or some poor customer just coming in to collect his bike." Carl's hand went from gently massaging Negan's arm to tracing patterns on his stomach to sliding down to grab the man's cock and give him a few firm strokes. "After you've closed for the day I bet we'd have some **real** fun. I'd love to get fucked on your favorite bike. That damn--What the fuck is it? Bonneville whatever the fuck. You pay that bike more attention than me!" Carl pouted as he narrowed his eyes and Negan chuckled before leaning up to peck his lips. "That's only my second favorite bike. My first favorite is my Harley Davidson, of fucking course." Negan corrected him before reaching down to place a hand over the younger boy's.

Negan wrapped an arm around Carl and brought him in for a long kiss, groaning as he tasted traces of himself on Carl's tongue. Carl continued stroking the man's cock at a steady pace, humming as he felt it hardening once again. The urge to suck Negan off again was strong, but he also really fucking wanted the man to be buried deep inside of him, filling him up.

"Negan," Carl whined after pulling away from the man. "I want you in me. Now." 

"Well aren't your balls huge as shit? Demanding shit from me like you're my god damn boss." Negan chuckled. Carl rolled his eyes. "My balls are only huge because they're filled with cum. Maybe you could fix that?"

Negan decided not to say anything as he sat up and grabbed Carl's arm. He pushed the boy so that he was on his stomach, facing the large mirror, and then straddled his legs. He squeezed Carl's ass cheeks before pulling them apart and letting out a low whistle. Carl's pretty pink hole was calling his fucking name.

Carl let out a desperate whine as Negan pushed a finger inside of him, curling it expertly before allowing it to slide out again. He repeated this process over and over again until Carl was fidgeting around underneath him and whining his name quietly, begging him for something more.

Negan worked his way up to three fingers, teasing Carl until he thought the boy was going to start sobbing right then and there, and then he readjusted their positions so that Carl was on all fours and he was between the boy's legs.

One second, Carl was desperately pushing his hips back, trying to line himself up with Negan's cock and finally get what he'd been waiting for seemingly forever, and the next, Negan was thrusting in and out of him wildly, his quick pace and brute force pushing the boy damn near off the bed.

Carl cried out as Negan's cock plunged in and out of him relentlessly and Negan grabbed Carl's neck, forcing his head backward. "Look at how damn pretty you are," Negan growled, eyeing Carl through the mirror. "You look so fucking good right now, baby. You always look good when I'm fucking the shit out of you, of fucking course."

"T-Thank you, daddy," Carl moaned. "Fuck! You're gonna make me cum again."

Negan grinned and slowed down his pace, making his thrusts deeper and reveling in the sound of Carl's desperate cries and constant cursing. He let go of the boy's neck and Carl lowered his upper body onto the bed, burying his face into the sheets. He felt warm all over, sweat dripping down his stomach and his skin getting even redder, if possible. Negan's slow thrusts were hitting his G-spot just right, and that along with the feeling of Negan's hands digging into his hips sent Carl over the edge.

Carl nearly screamed as his orgasm took over him, his body twitching as he tried to get away from and push himself closer to Negan's cock. The pleasure was almost too much, but he couldn't get enough of it. His senses were overwhelmed by Negan, and damn, Carl couldn't remember the last time he'd felt this good!

Negan's thrusts came to a complete stop and he pulled out of Carl before turning him over so that he was on his back. He stroked himself quickly smirking down at Carl who waited patiently with his tongue out. "Good boy," he whispered.

Carl moaned as Negan cum began spurting out quickly, some hitting his cheek, some landing on his chin, and most landing in his mouth. Negan's taste was distinct and delicious in a way that Carl just couldn't explain, and fuck was he happy that he was lucky enough to be the one who got to taste it so often.

Carl swallowed it all when Negan was done, even bringing a finger up to collect what had landed on his face and swallow that as well. Negan collapsed beside him and immediately pulled him closer, cuddling him despite the fact that they were both about to burn up.

"Shit, am I glad I decided to dress up for you." Carl chuckled. "I might just have to invest in an evening gown. How do you feel about that?"

"You do it and you won't leave this bedroom ever again."

**Author's Note:**

> Issa fucking lot going on in this, tbh. I had a lot of ideas and they all fit together nicely in this, I think! SMH one blowjob or less per work was my limit in the past because writing blowjobs is so difficult for me, but heyy we got it done! I had to include Carl sucking Negan off while handcuffed, the second I wrote about cuffs it was outta my hands. I hope you guys enjoyed! Thank you for reading. P.S sorry for any typos I proofread this once but then I added more to it and I'm not sure if I reproofed it after that so...


End file.
